TY - JOUR
T1 - Methanolysis of acetylated sugars and glycosides in the presence of tin oxides and alkoxides
AU - Herzig, Jacob
AU - Nudelman, Abraham
AU - Gottlieb, Hugo E.
PY - 1988/6/15
Y1 - 1988/6/15
N2 - A simple, regioselective O-deacetylation procedure is described which involves ≤0.5 equiv. of Bu3SnOMe or Bu2SnO in methanol. Anomeric acetates are considerably more reactive than primary and secondary acetates, thereby enabling selective removal, to give ∼70% of products with HO-1 unsubstituted. Prolonged reaction resulted in complete deacetylation. Secondary acetates were removed faster than primary acetates and the overall rates of reaction were influenced greatly by the anomeric substituent in the order of OAc {A figure is presented} OH ≫ OMe. No acyl migration took place under the reaction conditions.
AB - A simple, regioselective O-deacetylation procedure is described which involves ≤0.5 equiv. of Bu3SnOMe or Bu2SnO in methanol. Anomeric acetates are considerably more reactive than primary and secondary acetates, thereby enabling selective removal, to give ∼70% of products with HO-1 unsubstituted. Prolonged reaction resulted in complete deacetylation. Secondary acetates were removed faster than primary acetates and the overall rates of reaction were influenced greatly by the anomeric substituent in the order of OAc {A figure is presented} OH ≫ OMe. No acyl migration took place under the reaction conditions.
UR - http://www.scopus.com/inward/record.url?scp=0006091688&partnerID=8YFLogxK
U2 - 10.1016/0008-6215(88)85038-9
DO - 10.1016/0008-6215(88)85038-9
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AN - SCOPUS:0006091688
SN - 0008-6215
VL - 177
SP - 21
EP - 28
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - C
ER -